MacOs Catalina add music manually on iPhone 11

I have this problem too, I manually manage my Music library on my iMac 2015. After updating to Catalina I could no longer manually move music drag between the Music app and my plugged in iPhone. The iPhone icon to the left on the Music app didn't light up when I dragged music onto it.

I finally solved it.

Place the music you want to move into a new playlist on your Mac, then drag the playlist to the left hand iPhone devices entry in the Music app and its then allowed and loads OK. .

This must be a workaround to a Catalina bug, I can't believe it's intended as the only way to manually manage your music between mac and iPhone.

It works for me via Finder.

Step 1: make sure "Manually manage music and videos" is checked

Step 2: click on the iPhone icon in Finder, click on the "Music" tab and drag & drop your music onto the window: https://imgur.com/a/JtLuqi7

macOS Catalina - Version 10.15

I just updated to Catalina and updated my iPhone and have also discovered this problem. Thanks to all who wrote about this because I thought I was going crazy.

To everyone who suggests "Just turn on Manage Music manually" please stop. You're missing the point. Here's what I've discovered. Perhaps someone from Apple will take note? BTW - I'm writing " iTunes" in place of the new "MUSIC" name for the app.

• I can no longer Drag and Drop songs from iTunes into my iPhone, unless the songs have been in the library for a while. I have no clue why that is. If I download an album from Bandcamp and import it into iTunes, I can't then copy it into my iPhone via Drag and Drop. Also, the same issue occurs when I rip a newly purchased CD into iTunes.
• I can make a Playlist of the newly downloaded album (simply by dragging the entire album into the left sidebar of iTunes). Then I can drag and drop that playlist into the iPhone, but why in the world would anyone consider that an improvement? And why hide that information from users?
• For those who mentioned using a Right Click and choosing Add To Device -- again, that only seems to work with older tracks. With my newly ripped or downloaded tracks, Add to Device is either not available (if I'm clicking on the songs) or greyed out in the menu bar.
• Another weird thing - I can't Drag and Drop tracks from my Desktop into iTunes if I'm in the "Recently Added" window. I can Drag and Drop from my desktop to iTunes if I'm in the Songs window. Seems odd. MLately I've been using the menubar's IMPORT function instead when bringing a new album into iTunes.

BTW - I generally listen to entire albums, so making Playlists of select songs is not something I do. Perhaps Apple has forgotten that people purchase and listen to entire albums?

One more weird thing - this recent upgrade also changes how Apple's Carplay looks in my car. Generally, the improvements there are excellent. However, the need to import via Playlists into my iPhone has an unintended impact. Now, when I select Recently Added from the Music App in Carplay, all my new albums have two icons - one for the album and another from the Playlist of the album. So I only see half as many albums at once. That's annoying.

I have discovered that I can manually delete the Playlists from within my iPhone and it doesn't delete the song files. In fact, a user's ability to manage songs and playlists within the iPhone has improved, which is lucky because this screw up with the iTunes/Music app sucks big time. Something tells me the people who did this don't actually listen to full albums. They just build Playlists from lots of songs. If you do that, this might all seem fine.

I have not found any other workarounds that are reliable for this issue.

AHA! I was having this same problem but none of the solutions here worked for me (though I admit I skimmed). What ultimately fixed it for me was this:

1. Unplug your phone from your Mac.
2. On your iPhone go to: Settings > General > Reset > Reset Location & Privacy
3. Plug your phone back into your Mac. Click "Trust" When the "Trust this computer?" prompt appears.
4. On your Mac, "Trust" When the "Trust this iPhone?" prompt appears

I can now copy songs right from Catalina's Music app onto my iPhone. I hope this works for you!

I'm still not able to manually add music, even with the suggestions above.

In addition to not being able to drag-and-drop, the "Add to Device" item is grayed out in the "Song" menu even though my phone is attached and showing in the left pane under Devices.

I believe this is a bug. The expected behavior is that if your device is attached you should be able to manually add songs to that device (unless perhaps there is some copyright management, but that isn't the case here).

With 10.15.2 set to manually control music, click on your device in finder and select manual control. Open Apple Music and select Artist or Albums or what ever on the left, Highlight the songs that you want to copy across, drag them over to your device on the left and then click on your device and there they are.

The problem has been solved, I believe, but we've got to get our heads around it.

I'm also having this issue. I'm running Catalina version 10.15.4 and the Music App won't let me drag and drop certain songs to my iPhone XS Max which is up to date. The "Add to Device" option only appears for certain songs

I hope the Apple developers will fix this problem with the Catalina update Music app. We need to be able to see our playlists and songs on our iPhones from the application so that we can manage our iPhones more efficiently. This workaround seems like how Windows Media Center use to transfer Mp3 files to older MP3 players.

I hope they fix it as well. I prefer to manage the playlists on my iPhone via the app on my laptop. It's much easier. Now, I can't even see what playlists are on my iPhone via the laptop app. Moving things around on the actual iPhone is clunky and time consuming. :(

Plug your iphone in

Open finder

Scroll down on the side bar on the left hand side of the finder window until you see "Locations"

Click on your iphone

You'll have to "trust" the computer when prompted to do so on your iphone.

Once that process is complete open up the music app on your mac and you'll see your iphone under "devices" on the left hand side.

You can now manually drag and drop music into your iphone like before.

I have the same issue. I tried everything the folks below suggested with no luck. Even did the last Catalina update, still can't manage music manually. Can't add any music to my iPhone from my iMac. So no new Mobil music for me until this issue is fixed. iTunes worked so well for so long. Why change something just to change it? Especially if you can't make it work. Very frustrating Apple. Please figure this one out ASAP.

That's not the issue I'm having. Using the finder and seeing the iphone under "devices" in the music app is fine.

The issue I have is that's all I can see in the music app on my laptop. Just the iphone. It doesn't have a drop down that shows the playlists on the iphone so that I can edit them. I still see the playlists that are on my laptop but not the playlists on my iphone.

Editing the playlists on the iphone itself is laborious. Using the app (when it was iTunes) on the laptop is so much easier. I'm hoping they find a way to bring that option back. It's sorely missed.

For me it worked for only 1/2 devices.

iPhone 7 Plus worked fine.

iPad 2nd 12.9 doesn't work at all!!!

It is so frustrating, that I even tried deleting my music and importing it back and of course it wasn't syncing so it didn't delete any of the songs. But deleting them from the Settings App did delete everything, and since I can't sync the tablet... I have no music in my iPad!!!! (Palm in the face)

Thanks Apple (Sarcasm alert!)

I completely agree with Scott here. Also, if you go through the finder to manage your library on the phone, its also eliminated the ability to sort through your phone library by different categories like you could on iTunes. I have a large GB iPhone with a lot of music not purchased through iTunes or available on streaming. Catalina makes utilizing your libraries like this on your iPhone an almost impossible experience

I've tried this exact thing more than once. It appears to work when you click and drag but nothing transfers to the phone. I wonder what's different. I have the latest Catalina update and the latest iPhone update.